Your Situationship Hasn't Hit Its Vesting Cliff Yet. That's Exactly the Problem.
It is that time of year.
Hayes Valley — "Cerebral Valley" to anyone who's spent more than a week in San Francisco lately — is in the middle of another compensation supernova, with AI leads pulling $350K base plus equity packages that read like phone numbers, and two-bedrooms in the neighborhood now renting for $5,000 a month because nobody wants to commute when the hacker house down the block is where the next deal gets done. Everyone in this city is fluent in vesting schedules, term sheets, and burn rate. Almost nobody applies that fluency to their own dating life, where it would actually be useful.
Here's the thing nobody's saying out loud at the standing desk: your situationship is an unvested grant, and you've been treating it like fully owned equity for months.
San Francisco Dating, By the Numbers
The median age in San Francisco is 38, with a long-running gender imbalance in the 20s and 30s dating pool — more single men than women citywide, though the picture flips among college-educated singles specifically.
73% of San Francisco singles report work as their single biggest obstacle to dating.
AI-specialist compensation in the city has reached $350K+ base salaries with multi-million dollar equity packages, concentrated heavily in the Hayes Valley "Cerebral Valley" micro-market.
Two-bedroom rents in that same corridor have climbed to roughly $5,000 a month, up 16%+ year-over-year — a premium driven almost entirely by people who want to live where the deals happen.
Now let's read the cap table properly.
Grant: Situationship Vesting Schedule: Unclear — standard four-year, one-year cliff, or undefined entirely Employee: You, acting fully vested in something you don't actually own yet
The Term Sheet — "Verbally Agreed, Never Actually Signed"
A term sheet isn't binding. It's a statement of intent — the outline of a deal everyone's nodding along to, before anyone's actually committed anything in writing. Most situationships never get past this stage. Plenty of warm conversations about "where this is going," none of it ever formalized into something either party could actually be held to. Verbal alignment isn't a deal. It's a deal people are still deciding whether to make.
The Vesting Cliff — "Nothing Is Yours Until You Clear It"
Standard startup equity vests over four years with a one-year cliff — meaning if you leave, or get let go, before that first year is up, you walk away with zero, regardless of how good the work was. Most situationships operate on an identical, unspoken cliff: the first several months can be genuinely great and still mean nothing, structurally, if the thing ends before anyone actually clarifies what it is. Acting like six warm months equals ownership, before the cliff has even been discussed, is how people end up walking away with nothing they can point to.
Due Diligence — "Skipped Because the Pitch Was Good"
Real due diligence means checking the story against the facts — talking to references, verifying the numbers, finding out what the deck didn't mention. In a hot market, with a charismatic founder and a killer pitch, people skip it constantly, and it's almost always the deals that skipped diligence that later implode. A situationship where you've never actually met their friends, never seen how they handle a bad week, never checked anything beyond what they've presented, is an investment made entirely on the pitch.
Down Round — "Same Company, Worse Terms, Nobody Wants to Say It Out Loud"
A down round happens when a company raises money at a lower valuation than its last round — a quiet, often unspoken admission that the previous price was wrong. Situationships have the exact same moment, usually around month five or six: the energy that justified the early enthusiasm has quietly dropped, but neither person wants to be the one to mark down the valuation out loud, so everyone just keeps operating off the old, inflated number.
Here's what every operator in this city already understands about capital and somehow forgets to apply to their own relationships: enthusiasm is not the same as terms. A great pitch, a great vibe, a genuinely exciting first few months — none of it is enforceable until somebody actually puts something in writing and both sides clear the cliff.
Most San Francisco situationships are unvested grants being treated like liquid equity. A few good nights in the Mission or a long walk through Dolores Park feel like proof of value. They're a term sheet. They were never the signed agreement.
That's most of what an actual matchmaker does here that a hacker house full of opinions and a charismatic pitch cannot — someone outside the deal, doing the actual diligence, willing to say "this hasn't vested" instead of letting you act like founder-level conviction is the same thing as an executed contract.
The cliff is still ahead. The real question is whether your situationship is actually heading toward it — or whether you've just been counting unvested shares as a win.